Methanol → HCID 67485985, compound

HRID 642807Notes

Reaction equation

HRID 642807 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.CO.[OH-].[Na+]>CCOC(C)=O>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:17][CH:18]=2)=[CH:27][CH:26]=1)([CH3:30])([CH3:31])[CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 674879154-[1-(4'-tert-Butyl-biphenyl-4-ylamino)-3-methyl-butyl]-benzoic acid methyl ester

Product 1

HCID 67485985HCID 67485985, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[1-(4′-tert-Butyl-biphenyl-4-ylamino)-3-methyl-butyl]-benzoic acid methyl ester (718 mg) is taken into MeOH (10 mL), followed by the addition of 5N NaOH (1 mL). The reaction is stirred for 4 h, diluted with EtOAc, washed with aqueous HCl and brine. The organic portion is dried over MgSO4, and concentrated to afford 510 mg of the titled compound, which is used directly in the next step.

Workup

  1. washwashed with aqueous HCl and brine
  2. dry with materialThe organic portion is dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0cdd80fdab0e4dd0a20c0168d9b0edb9
Source dataset
uspto-grants-2010_04
Patent number
US07696248B2

Reaction notes

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